Methanesulfonamide → 5-Chloro-2-fluoro-4-methyl-N-(methylsulfonyl)benzamide
Reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:13][S:14]([NH2:17])(=[O:16])=[O:15].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:17][S:14]([CH3:13])(=[O:16])=[O:15])=[O:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 30 °C
Procedure
To 5-chloro-2-fluoro-4-methylbenzoic acid (200 g, 1.06 mol) in DCM (1.4 L) was added methanesulphonamide (152 g, 1.6 mol), 4-(dimethylamino)pyridine (183 g 1.6 mol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (306 g, 1.6 mol). The reaction mixture spontaneously heated at 30° C. over 30 minutes, then it was stirred at room temperature for 18 hours under a nitrogen atmosphere. The reaction was washed with aqueous hydrochloric acid (4 M, 0.8 L). The organic layer was separated, washed with water (500 mL), dried over sodium sulphate and concentrated in vacuo to yield a tan solid, which was recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL) and cooling to yield the title compound (118 g, 45%).
Workup
- washThe reaction was washed with aqueous hydrochloric acid (4 M, 0.8 L)
- customThe organic layer was separated
- washwashed with water (500 mL)
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
- customto yield a tan solid, which
- customwas recrystallised from hot EtOAc (0.9 L) by addition of n-heptane (100 mL)
- temperaturecooling
Sources & evidence
- ORD record
- ord-6303fbf709fc481ba7924e3bf9d6f31b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685977B2
Reaction notes
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